# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

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# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_vol34

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'cadmium sulfonyldibenzoate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 Cd O6 S, 0.36(O2), 0.72(O)'
_chemical_formula_sum            'C14 H8 Cd O7.44 S'
_chemical_formula_weight         439.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -1.4396 0.7832 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.0826 0.0763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.3382(4)
_cell_length_b                   21.4986(7)
_cell_length_c                   10.1527(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.0000(10)
_cell_angle_gamma                90.00
_cell_volume                     2900.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.014
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1723.8
_exptl_absorpt_coefficient_mu    2.011
_exptl_absorpt_correction_type   'multi-scan '
_exptl_absorpt_correction_T_min  0.9319
_exptl_absorpt_correction_T_max  0.9823
_exptl_absorpt_process_details   'SADABS (Shieldrick 2008)'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.41328
_diffrn_radiation_type           ?
_diffrn_radiation_source         Synchrotron
_diffrn_radiation_monochromator  silicon
_diffrn_measurement_device_type  APEXII
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.4962
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6850
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         17.17
_reflns_number_total             4342
_reflns_number_gt                3853
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       APEXII
_computing_cell_refinement       APEXII
_computing_data_reduction        APEXII
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalMaker (CrystalMaker, 2009)'
_computing_publication_material  SHELXL97

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0001P)^2^+118.0839P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4342
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1622
_refine_ls_wR_factor_gt          0.1606
_refine_ls_goodness_of_fit_ref   1.215
_refine_ls_restrained_S_all      1.215
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1033(4) 0.7198(3) 0.7546(6) 0.0135(10) Uani 1 1 d . . .
C4 C 0.2599(5) 0.8031(3) 0.7541(7) 0.0167(12) Uani 1 1 d . . .
C2 C 0.1367(9) 0.7365(5) 0.6357(11) 0.022(2) Uani 0.70(2) 1 d P A 1
H2 H 0.1082 0.7198 0.5566 0.027 Uiso 0.70(2) 1 calc PR A 1
C3 C 0.2156(9) 0.7798(5) 0.6382(12) 0.026(3) Uani 0.70(2) 1 d P A 1
H3 H 0.2383 0.7929 0.5588 0.031 Uiso 0.70(2) 1 calc PR A 1
C5 C 0.2215(10) 0.7859(7) 0.8749(13) 0.029(3) Uani 0.70(2) 1 d P A 1
H5 H 0.2492 0.8029 0.9541 0.035 Uiso 0.70(2) 1 calc PR A 1
C6 C 0.1424(10) 0.7436(6) 0.8752(12) 0.029(3) Uani 0.70(2) 1 d P A 1
H6 H 0.1167 0.7317 0.9537 0.035 Uiso 0.70(2) 1 calc PR A 1
C2' C 0.1713(17) 0.7145(11) 0.660(2) 0.011(4) Uiso 0.30(2) 1 d P A 2
H2' H 0.1638 0.6834 0.5961 0.013 Uiso 0.30(2) 1 calc PR A 2
C3' C 0.2514(16) 0.7563(10) 0.662(2) 0.010(4) Uiso 0.30(2) 1 d P A 2
H3' H 0.2989 0.7525 0.6002 0.012 Uiso 0.30(2) 1 calc PR A 2
C5' C 0.195(2) 0.8092(16) 0.846(3) 0.027(6) Uiso 0.30(2) 1 d P A 2
H5' H 0.2046 0.8405 0.9094 0.032 Uiso 0.30(2) 1 calc PR A 2
C6' C 0.113(2) 0.7691(15) 0.848(3) 0.024(6) Uiso 0.30(2) 1 d P A 2
H6' H 0.0652 0.7745 0.9091 0.029 Uiso 0.30(2) 1 calc PR A 2
C7 C 0.3466(4) 0.8475(3) 0.7522(7) 0.0166(12) Uani 1 1 d . A .
C8 C 0.3628(4) 1.0173(3) 0.8044(6) 0.0130(10) Uani 1 1 d . . .
C9 C 0.2726(4) 1.0593(3) 0.7927(6) 0.0140(11) Uani 1 1 d . . .
C10 C 0.2384(5) 1.0820(3) 0.6681(7) 0.0176(12) Uani 1 1 d . . .
H10 H 0.2716 1.0718 0.5942 0.021 Uiso 1 1 calc R . .
C11 C 0.1540(5) 1.1201(3) 0.6559(7) 0.0190(12) Uani 1 1 d . . .
H11 H 0.1304 1.1358 0.5737 0.023 Uiso 1 1 calc R . .
C12 C 0.1051(4) 1.1346(3) 0.7678(7) 0.0155(11) Uani 1 1 d . . .
C13 C 0.1382(5) 1.1117(3) 0.8916(7) 0.0185(12) Uani 1 1 d . . .
H13 H 0.1045 1.1215 0.9652 0.022 Uiso 1 1 calc R . .
C14 C 0.2227(5) 1.0737(3) 0.9033(7) 0.0176(12) Uani 1 1 d . . .
H14 H 0.2460 1.0578 0.9856 0.021 Uiso 1 1 calc R . .
Cd1 Cd 0.51548(3) 0.926968(19) 0.91945(4) 0.00920(12) Uani 1 1 d . . .
O1 O 0.3851(3) 0.9906(2) 0.7035(5) 0.0161(9) Uani 1 1 d . . .
O2 O 0.4100(3) 1.0095(2) 0.9191(4) 0.0131(8) Uani 1 1 d . . .
O1W O -0.024(5) 0.963(3) 0.806(6) 0.29(5) Uiso 0.72(11) 1 d P . .
O3 O 0.3789(3) 0.8710(2) 0.8607(5) 0.0181(9) Uani 1 1 d . . .
O2W O 0.0000 0.898(5) 0.7500 0.32(7) Uiso 0.81(17) 2 d SP . .
O4 O 0.3802(4) 0.8568(2) 0.6406(5) 0.0201(10) Uani 1 1 d . . .
O5 O 0.0046(3) 0.6338(2) 0.8725(5) 0.0142(8) Uani 1 1 d . . .
O6 O 0.0045(4) 1.2183(2) 0.6280(6) 0.0231(10) Uani 1 1 d . . .
S1 S 0.0000 0.66852(9) 0.7500 0.0111(4) Uani 1 2 d S . .
S2 S 0.0000 1.18504(10) 0.7500 0.0170(4) Uani 1 2 d S . .
O3W O 0.036(4) 0.945(2) 0.915(5) 0.10(2) Uiso 0.31(5) 1 d P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.011(2) 0.011(2) 0.019(3) -0.001(2) 0.004(2) -0.002(2)
C4 0.011(2) 0.010(2) 0.029(3) 0.000(2) 0.002(2) -0.003(2)
C2 0.021(5) 0.021(5) 0.025(5) 0.000(4) 0.001(4) -0.009(4)
C3 0.022(5) 0.022(5) 0.035(6) 0.009(4) 0.005(4) -0.008(4)
C5 0.026(6) 0.030(7) 0.032(6) -0.014(5) 0.010(5) -0.019(5)
C6 0.033(6) 0.034(7) 0.022(5) -0.016(5) 0.017(5) -0.020(6)
C7 0.010(2) 0.009(2) 0.031(4) -0.001(2) 0.001(2) -0.0036(19)
C8 0.010(2) 0.012(2) 0.017(3) 0.003(2) 0.002(2) 0.0009(19)
C9 0.010(2) 0.013(3) 0.019(3) 0.001(2) 0.002(2) 0.0013(19)
C10 0.016(3) 0.021(3) 0.017(3) 0.006(2) 0.005(2) 0.003(2)
C11 0.017(3) 0.020(3) 0.020(3) 0.008(2) 0.004(2) 0.002(2)
C12 0.010(2) 0.012(3) 0.024(3) 0.004(2) 0.000(2) 0.001(2)
C13 0.016(3) 0.018(3) 0.023(3) -0.003(2) 0.006(2) 0.001(2)
C14 0.015(3) 0.018(3) 0.020(3) 0.000(2) 0.002(2) 0.001(2)
Cd1 0.00886(19) 0.00808(19) 0.0107(2) -0.00123(14) 0.00129(13) 0.00053(14)
O1 0.017(2) 0.014(2) 0.018(2) -0.0007(17) 0.0042(17) 0.0039(16)
O2 0.0132(19) 0.0120(19) 0.014(2) 0.0002(15) -0.0013(15) 0.0012(15)
O3 0.016(2) 0.012(2) 0.026(2) 0.0049(17) 0.0016(18) -0.0040(16)
O4 0.015(2) 0.013(2) 0.032(3) -0.0017(19) 0.0074(19) -0.0033(17)
O5 0.017(2) 0.0103(18) 0.016(2) 0.0036(15) 0.0024(16) 0.0006(15)
O6 0.019(2) 0.016(2) 0.034(3) 0.009(2) 0.002(2) 0.0009(18)
S1 0.0119(8) 0.0084(8) 0.0134(9) 0.000 0.0034(7) 0.000
S2 0.0117(9) 0.0110(9) 0.0284(12) 0.000 0.0015(8) 0.000

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.370(12) . ?
C1 C2' 1.38(2) . ?
C1 C6 1.387(13) . ?
C1 C6' 1.42(3) . ?
C1 S1 1.762(6) . ?
C4 C5' 1.33(3) . ?
C4 C3 1.365(14) . ?
C4 C3' 1.37(2) . ?
C4 C5 1.419(14) . ?
C4 C7 1.501(8) . ?
C2 C3 1.404(13) . ?
C5 C6 1.393(14) . ?
C2' C3' 1.40(3) . ?
C5' C6' 1.40(4) . ?
C7 O3 1.254(8) . ?
C7 O4 1.270(9) . ?
C8 O1 1.233(8) . ?
C8 O2 1.286(7) . ?
C8 C9 1.500(8) . ?
C9 C14 1.390(9) . ?
C9 C10 1.395(9) . ?
C10 C11 1.388(9) . ?
C11 C12 1.394(9) . ?
C12 C13 1.386(9) . ?
C12 S2 1.770(6) . ?
C13 C14 1.389(9) . ?
Cd1 O4 2.175(5) 2_656 ?
Cd1 O3 2.220(5) . ?
Cd1 O2 2.264(4) . ?
Cd1 O2 2.293(4) 5_677 ?
Cd1 O1 2.341(5) 2_656 ?
Cd1 O5 2.518(4) 7_567 ?
Cd1 Cd1 3.4296(9) 2_656 ?
O1 Cd1 2.341(4) 2_656 ?
O2 Cd1 2.293(4) 5_677 ?
O1W O1W 1.36(10) 2_556 ?
O1W O3W 1.37(7) . ?
O1W O2W 1.56(7) . ?
O2W O1W 1.56(7) 2_556 ?
O4 Cd1 2.175(5) 2_656 ?
O5 S1 1.447(4) . ?
O5 Cd1 2.518(4) 7_567 ?
O6 S2 1.436(5) . ?
S1 O5 1.447(4) 2_556 ?
S1 C1 1.762(6) 2_556 ?
S2 O6 1.436(5) 2_556 ?
S2 C12 1.770(6) 2_556 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C2' 29.1(9) . . ?
C2 C1 C6 123.8(8) . . ?
C2' C1 C6 115.2(11) . . ?
C2 C1 C6' 112.2(13) . . ?
C2' C1 C6' 120.1(15) . . ?
C6 C1 C6' 29.6(11) . . ?
C2 C1 S1 117.0(6) . . ?
C2' C1 S1 119.3(9) . . ?
C6 C1 S1 119.1(6) . . ?
C6' C1 S1 120.4(12) . . ?
C5' C4 C3 112.4(15) . . ?
C5' C4 C3' 122.1(17) . . ?
C3 C4 C3' 30.5(9) . . ?
C5' C4 C5 27.8(12) . . ?
C3 C4 C5 119.2(8) . . ?
C3' C4 C5 112.7(10) . . ?
C5' C4 C7 119.6(15) . . ?
C3 C4 C7 119.9(7) . . ?
C3' C4 C7 118.3(10) . . ?
C5 C4 C7 120.9(7) . . ?
C1 C2 C3 117.3(9) . . ?
C4 C3 C2 121.8(10) . . ?
C6 C5 C4 120.2(10) . . ?
C1 C6 C5 117.7(10) . . ?
C1 C2' C3' 119.1(17) . . ?
C4 C3' C2' 119.8(17) . . ?
C4 C5' C6' 120(3) . . ?
C5' C6' C1 118(2) . . ?
O3 C7 O4 126.8(6) . . ?
O3 C7 C4 116.8(6) . . ?
O4 C7 C4 116.4(6) . . ?
O1 C8 O2 123.8(6) . . ?
O1 C8 C9 117.7(6) . . ?
O2 C8 C9 118.5(6) . . ?
C14 C9 C10 120.9(6) . . ?
C14 C9 C8 120.5(6) . . ?
C10 C9 C8 118.6(6) . . ?
C11 C10 C9 119.1(6) . . ?
C10 C11 C12 119.5(6) . . ?
C13 C12 C11 121.7(6) . . ?
C13 C12 S2 119.8(5) . . ?
C11 C12 S2 118.5(5) . . ?
C12 C13 C14 118.6(6) . . ?
C13 C14 C9 120.2(6) . . ?
O4 Cd1 O3 94.54(19) 2_656 . ?
O4 Cd1 O2 162.85(18) 2_656 . ?
O3 Cd1 O2 85.92(16) . . ?
O4 Cd1 O2 111.43(18) 2_656 5_677 ?
O3 Cd1 O2 144.01(18) . 5_677 ?
O2 Cd1 O2 76.41(17) . 5_677 ?
O4 Cd1 O1 81.37(17) 2_656 2_656 ?
O3 Cd1 O1 131.53(17) . 2_656 ?
O2 Cd1 O1 85.51(16) . 2_656 ?
O2 Cd1 O1 78.60(16) 5_677 2_656 ?
O4 Cd1 O5 89.60(17) 2_656 7_567 ?
O3 Cd1 O5 78.42(16) . 7_567 ?
O2 Cd1 O5 107.24(15) . 7_567 ?
O2 Cd1 O5 77.34(15) 5_677 7_567 ?
O1 Cd1 O5 149.06(16) 2_656 7_567 ?
O4 Cd1 Cd1 75.09(14) 2_656 2_656 ?
O3 Cd1 Cd1 72.93(13) . 2_656 ?
O2 Cd1 Cd1 88.73(11) . 2_656 ?
O2 Cd1 Cd1 136.38(11) 5_677 2_656 ?
O1 Cd1 Cd1 59.28(12) 2_656 2_656 ?
O5 Cd1 Cd1 146.03(11) 7_567 2_656 ?
C8 O1 Cd1 154.7(4) . 2_656 ?
C8 O2 Cd1 111.1(4) . . ?
C8 O2 Cd1 135.8(4) . 5_677 ?
Cd1 O2 Cd1 103.59(17) . 5_677 ?
O1W O1W O3W 113(8) 2_556 . ?
O1W O1W O2W 64(2) 2_556 . ?
O3W O1W O2W 85(4) . . ?
C7 O3 Cd1 131.7(4) . . ?
O1W O2W O1W 52(5) . 2_556 ?
C7 O4 Cd1 130.1(4) . 2_656 ?
S1 O5 Cd1 171.5(3) . 7_567 ?
O5 S1 O5 117.9(4) 2_556 . ?
O5 S1 C1 109.0(3) 2_556 2_556 ?
O5 S1 C1 108.7(3) . 2_556 ?
O5 S1 C1 108.7(3) 2_556 . ?
O5 S1 C1 109.0(3) . . ?
C1 S1 C1 102.6(4) 2_556 . ?
O6 S2 O6 120.2(5) 2_556 . ?
O6 S2 C12 107.5(3) 2_556 2_556 ?
O6 S2 C12 108.1(3) . 2_556 ?
O6 S2 C12 108.1(3) 2_556 . ?
O6 S2 C12 107.5(3) . . ?
C12 S2 C12 104.3(4) 2_556 . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        17.17
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         2.153
_refine_diff_density_min         -2.233
_refine_diff_density_rms         0.269
_database_code_depnum_ccdc_archive 'CCDC 937289'